O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 2-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate

HRID 642746Notes

Reaction equation

HRID 642746 reaction equation
[C:1]([O:9][CH:10]1[CH2:16][CH2:15][CH:14]2[CH:11]1[CH2:12][C:13]2=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:30])(=O)=O>C(Cl)Cl>[C:1]([O:9][CH:10]1[CH:11]2[CH:14]([C:13](=[O:17])[NH:30][CH2:12]2)[CH2:15][CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][CH:10]1[CH:11]2[CH:14]([NH:30][C:13](=[O:17])[CH2:12]2)[CH2:15][CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 592595756-Oxobicyclo[3.2.0]heptan-2-yl benzoate

Product 2

HCID 592595601-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoateHCID 592595712-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoateYield 133.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of compound 1H (500 mg, 2.2 mmol) in CH2Cl2 (5 mL) was added a solution of O-mesitylenesulfonylhydroxylamine (650 mg, 3 mmol) in CH2Cl2 (2 mL) at −10° C., and the stirring was continued for 20 min between −10 to 0° C. It was concentrated, added to a mixed solvent of benzene and methanol (30 mL, 3:1) followed by a slurry of basic alumina (25 g) in methanol (20 mL). The reaction mixture was stirred at RT overnight, and alumina solid was removed by filtration. Purification by silica gel chromatography (5% to 100% EtOAc in hexanes, then 5% methanol in EtOAc) provide mixtures of the title compounds 1I and 1J (total 360 mg) as a yellow oil. MS (ES) m/z 246 [M+H]+.

Workup

  1. concentrationIt was concentrated
  2. additionadded to a mixed solvent of benzene and methanol (30 mL, 3:1)
  3. customalumina solid was removed by filtration
  4. customPurification by silica gel chromatography (5% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-ff4911748c5a40cb91eab397b5486820
Source dataset
uspto-grants-2010_04
Patent number
US07696241B2

Reaction notes

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